Month: November 2020

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 22236-10-8, name is 4-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 22236-10-8

1-[(6-AMINOPYRIDIN-3-YL) METHYL]-3-{[4-(DIFLUOROMETHOXY) phenyl] AMINO} ? 4-PHENYL- 1H-PYRROLE-2, 5-dione A mixture OF TERT-BUTYL {5- [ (3-CHLORO-2, 5-dioxo-4-phenyl-2, 5-dihydro-1H-pyrrol-1- yl) methyl] PYRIDIN-2-YL} CARBAMATE (0.70 g, 1.7 mmol) and 4- (difluoromethoxy) aniline (0.54 g, 3.4 mmol) in DMF (4 mL) was heated in a microwave reactor at 150C for 8 min.. The solvent was evaporated and the residue was purified on a pre-packed SIO2COLUMN (ISOLUTE0 SI, lOg/70 mL) using CH2C12 and then CH30HL CH2CL2 (1: 99,2 : 98 and then 5: 95) as eluant to give 0.4 g (54%) of the title COMPOUND. 1H NMR (400 MHz, CDC13) 8 7.99 (bs, 1H), 7.67-7. 62 (m, 2H), 7.14-7. 04 (m, 3H), 6.91 (d, J =8 Hz, 2H), 6.78 (d, J=8 Hz, 1H), 6.72 (d, J=9 Hz, 2H), 6.63 (d, J=9 Hz, 2H), 6.33 (t, J=74 Hz, 1H) and 4.60 (s, 2H).

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/5416; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 75148-49-1, 75148-49-1

To a solution of 3-bromobenzylaldehyde diethyl acetal (0.518 g, 2.0 mmol) and15 anhydrous toluene (4 ml) was added 1-methylpiperazine (0.240 g, 2.4 mmol) followedby Pd2(dba)3 (0.018 g, 0.02 mmol), racemic BINAP (0.037 g, 0.06 mmol) and Na01Bu(0.326 g, 3.4 mmol). The reaction mixture was placed into an oil bath preheated to 100C and stirred at this temperature for 18 h under argon, then allowed to cool to roomtemperature. Aqueous HCI (1M; 10 ml) was added, the mixture was vigorously stirred20 for 2.5 h, then the pH adjusted to 13 with 6M aqueous NaOH and extracted with ethylacetate (3 x 30 ml). The combined organics were dried (Na2S04), concentrated in vacuoand the residue was absorbed on silica gel and placed on a 10 g isolute column. Elutionwith ethyl acetate I dichloromethane (v/v; 4:1) and then a gradient of methanol (3 to 7%)in ethyl acetate afforded the title compound as a yellow oil (0.170 g, 42%). 1 H-NMR (50025 MHz, DMSO-d6) 2.22 (s, 3H, N-Me), 2.46 (t, J = 5.0 Hz, 4H, piperazine C-H), 3.21 (t, J =5.1 Hz, 4H, piperazine C-H), 7.28 (m, 2H, PhH), 7.41 (m, 2H, PhH), 9.94 (s, 1 H, CHO);[00122] LC- MS (ESI, m/z): Rt = 0.86 min- 205 (M+Ht.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Bromobenzaldehyde Diethyl Acetal, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BLAGG, Julian; BAVETSIAS, Vassilios; MOORE, Andrew S.; LINARDOPOULOS, Spyridon; WO2013/190320; (2013); A1;,
Ether – Wikipedia,
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Adding some certain compound to certain chemical reactions, such as: 22236-10-8, name is 4-(Difluoromethoxy)aniline, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 22236-10-8. 22236-10-8

Into a 250-mL round-bottom flask purged with and maintained under nitrogen was placed 4- (difluoromethoxy)benzenamine (10 g, 62.8 mmol), ACN (100 mL), and BS (5.59 g, 31.4 mmol). The resulting solution was stirred for 1 h RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with a gradient of ethyl acetate/petroleum ether (1 :20 to 1 : 10). This resulted in 7.9 g (53%) of the title compound as red oil. MS-ESI: 238.0/240.0 (M+l).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4-(Difluoromethoxy)aniline.

Reference:
Patent; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (783 pag.)WO2019/23147; (2019); A1;,
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366-99-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

28.a. 1-(2-amino-4-fluoro-5-methoxyphenyl)-1-propanone (This product is obtained according to Sugasawa T; Toyoda T; Adachi M; Sasakura K, J Am. Chem. Soc., 100 (1978), p.4842-4852). Boron trichloride (1M in heptane, 156 ml, 156 mmol) is added dropwise, under an argon atmosphere at 0¡ã C. to a solution of 3-fluoro-4-methoxy-aniline (20 g, 142 mmol) in anhydrous dichloromethane (200 ml). The pink suspension thus obtained is maintained under agitation for 5 minutes, then propionitrile (33 ml, 420 mmol) is added dropwise followed by aluminium trichloride (20.8 g, 156 mmol) in small portions. The reaction medium is heated under reflux for 3 hours, cooled down to 0¡ã C., hydrolyzed by cautiously adding 2N hydrochloric acid (100 ml), then heated at reflux for 45 minutes. After cooling down to 0¡ã C. a precipitate is obtained which is filtered out, washed with dichloromethane, then taken up in water (300 ml). The aqueous phase is basified to an alkaline pH, extracted with dichloromethane then ethyl acetate. The organic phase is dried (MgSO4) then evaporated to produce a crude product which is purified by column chromatography (SiO2, AcOEt/Hpt: 1/99 to 20/80). 15.3 g of a yellow solid is obtained. NMR-1H (CDCl3): 1.20 (t, 3H); 2.92 (q, 2H); 3.83 (s, 3H); 6.2 (s, 2H); 6.40 (d, 2H); 7.32 (d, 2H). IR(KBr): 857; 1148; 1240; 1561; 1583; 1662.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Bigg, Dennis; Lavergne, Olivier; Pla Rodas, Francesc; Pommier, Jacques; Ulibarri, Gerard; Harnett, Jerry; Rolland, Alain; Liberatore, Anne-Marie; Lanco, Christophe; Cazaux, Jean-Bernard; Le Breton, Christine; Manginot, Eric; US2003/4150; (2003); A1;,
Ether – Wikipedia,
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Adding some certain compound to certain chemical reactions, such as: 6346-09-4, name is 4,4-Diethoxybutan-1-amine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6346-09-4. 6346-09-4

To a solution of [4,4-bis(ethyloxy)butyl]amine (5.0 g, 30.0 mmol) and Et3N (4.61 ml, 33.0 mmol) in 40 ml_ of THF was added ethyl 1 ,3-dioxo-1 ,3-dihydro-2/-/-isoindole-2- carboxylate (6.9 g, 32.0 mmol). The mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the residue was extracted with hexane. The hexane solution was concentrated in vacuo and heated at 100 0C under reduced pressure to remove ethylcarbamate by sublimation. The mixed solution of diethyl acetal (2.0 g, 6.95 mmol) thus obtained and 1 Lambda/aq. HCI (14 ml_) in acetone (20 ml_) was heated under reflux for 15 min. Acetone was evaporated and aqueous layer was extracted with ether, dried over MgSO4, and filtered. The solvent was evaporated and the residue was moved to next step.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4,4-Diethoxybutan-1-amine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/30761; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

710-18-9, The chemical industry reduces the impact on the environment during synthesis 710-18-9, name is 1-Methoxy-4-(trifluoromethoxy)benzene, I believe this compound will play a more active role in future production and life.

PREPARATION 18 2-Methoxy-5-trifluoromethoxybenzoyl chloride Combine 2-methoxy-5-trifluoromethoxybenzene (1.0 g, 5.2 mmol) and trifluoroacetic acid (200 mL). Add slowly portionwise hexamethylenetetraamine (26 g, 185.7 mmol). Heat at 60 C. After 24 hours, cool to ambient temperature and pour the reaction mixture into a 2M aqueous solution of sulfuric acid (500mL). Cool and extract ten times with diethyl ether. Dry the combined organic layers over Na2 SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluding with 1/4 ethyl acetate/hexane to give 2-methoxy-5-trifluoromethoxybenzaldehyde.

The chemical industry reduces the impact on the environment during synthesis 1-Methoxy-4-(trifluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoechst Marion Roussel, Inc.; US5922737; (1999); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A common heterocyclic compound, 437-83-2, name is 3-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 437-83-2.

Step D: 1-bromo-3-fluoro-2-methoxybenzene: NaN02 (12.0 g, 173 mmol, in 40 mL of water)solution was added dropwise to the mixture of 3-fluoro-2-methoxyaniline (20.0 g, 158 mmol) in 200 mL of hydrobromic acid ( 4 7 %) and 100 mL of water at -5 ~ 0 C and stirred for 1 hour.This solution was then added slowly to the suspension ofCuBr (45.2 g, 315 mmol) in 50 mL ofhydrobromic acid (47 %) at 0 C. The resulting mixture was stirred at 0 C for 1 hour thenwarmed to 50 C and stirred for 1 hour. The reaction mixture was poured into ice water and extracted with ether (2 X 500 mL). The combined organic layer was washed with brine, driedover anhydrous Na2S04 and concentrated to give 1-bromo-3-fluoro-2-methoxybenzene.

The synthetic route of 3-Fluoro-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; WO2013/28474; (2013); A1;,
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Some common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, molecular formula is C7H4BrF3O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 64115-88-4

Preparation of (2-[trifluoromethoxylphenyl)fphenyl)phosphine chloride To a flame dried Schlenk tube containing magnesium turnings (0.15 g, 6.22 mmo) in anhydrous THF (7 mi) was added 1-bromo-2- [trifluoromethoxy] benzene (1.0 g, 4.14 mmo). An exothermic reaction ensued. Stirring was continued at room temperature. Once the reaction exotherm had dissipated, the reaction mixture was used in the next step as described beiow: The Grignard reagent (separated from excess Mg) was incrementally added to a solution of PhPCI2 (0.74 g, 4.14 mmol) in anhydrous THF (10 ml) at -78C. Once addition was complete, the reaction was stirred at room temperature for a further 20 min after which the reaction was complete as judged by 3 P NMR ( 1P NMR (CDCIs): delta 72.27 (m); 61.81 (m)). The product was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64115-88-4, its application will become more common.

Reference:
Patent; SASOL TECHNOLOGY (PROPRIETARY) LIMITED; MOGOROSI, Moses Mokgolela; MAUMELA, Munaka Christopher; OVERETT, Matthew James; WO2014/181248; (2014); A1;,
Ether – Wikipedia,
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5961-59-1, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5961-59-1, name is 4-Methoxy-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A round-bottomed flask was charged with the aryl halide (1 mmol),the indoline or (het)aryl amine (1 mmol), and Pd2(dba)3 (0.005mmol, 5 mg). At this point, CH2Cl2 (10 mL) was used to dissolve the reactants and to suspend K2CO3 (4 mmol, 552 mg) and Al2O3 (2g). The CH2Cl2 was then removed under reduced pressure and subsequently recovered. The residual powder was ground with a mortar and pestle for 5 min. A microwave oven reactor was charged with the reactant powder which was compacted as much as possible. The powder was heated at 140 ¡ãC for 20 min at medium power (350 W) ,then charged into a flash silica gel column which was eluted with hexane?EtOAc (4:1) to give the purified product. The solid products were further purified by crystallization from hexane?Et2O.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Basolo, Luca; Bernasconi, Alice; Broggini, Gianluigi; Gazzola, Silvia; Beccalli, Egle M.; Synthesis; vol. 45; 22; (2013); p. 3151 – 3156;,
Ether – Wikipedia,
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767-91-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 767-91-9 as follows.

General procedure: A mixture of aldehyde (1.97 mmol), amine (1.97 mmol), acetylene (2.95 mmol), and thecorresponding supported Au catalyst (1% wt, 60 mg, 0.002 mmol) was heated at 60 C for 8 h,after which time the solution was cooled and the catalyst was removed by filtration. The filtrate wasevaporated under reduced pressure to afford propargylamine 5. Yields were determined by integration of the 1H-NMR spectra of the crude reaction mixtures. After separation and washing with n-pentane,the catalyst was reused intact for the next reaction without any further pre-treatment.

According to the analysis of related databases, 2′-Methoxyphenyl acetylene, the application of this compound in the production field has become more and more popular.

Reference:
Article; Soengas, Raquel; Navarro, Yolanda; Iglesias, Maria Jose; Lopez-Ortiz, Fernando; Molecules; vol. 23; 11; (2018);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem